Synthesis of steroids



United States Patent SYNTHESIS or STEROIDS Gordon H. Thomas, New Brunswick, and Josef Fried, Princeton, N. J., assignors to Olin Mathieson Chemical (Iorporation, New York, N. Y., a corporation of Virginia No Drawing. Application December 6, 1957 Serial No. 700,943

1 Claim. (Cl. 260-23955) This invention relates to the synthesis of steroids and has for its object the provision of a new steroid of the formula CH3 H -"CHs even date herewith) with hydrogen fluoride.

The following example illustrates the invention:

2 EXAMPLE Hydrogen fluoride is bubbled into a stirred solution of 290 mg. of 95,115-epoxy-11a,l7a-dimethyltestosterone in 10 m1. of chloroform and 0.5 m1. of absolute ethanol at 0 C. The reaction mixture becomes cherry red in color and two phases are formed. At this point, passage of hydrogen fluoride is discontinued and the mixture is stirred at 0 C. for 80 minutes. The solution is neutralized by the careful addition of a suspension of sodium bicarbonate in water, and the steroids are then extracted with chloroform. The chloroform extract is washed with water, dried over sodium sulfate and evaporated to dryness in vacuo. The residue is dissolved in ml. of benzene and absorbed on 3 g. of acid-washed alumina. Elution with chloroform-benzene (1 :9; 250 ml.) followed by crystallization from acetone-hexane gives about 44mg. of 9oc-fll10I0-1 1 a, 17 a, 17 ,B-trimethyl-l 118, 14fl-epoxy1 8-nor- 18-iso-A -androstene-3-one, M. P. about 156-158" C.; [06]D+48.5 (c, 1.11 in chloroform);

Analysis.Calcd. for C H O F (332.44): C, 75.87; H, 8.79; F, 5.72. Found: C, 75.49; H, 8.64; F, 5.86.

The invention may be variously otherwise embodied within the scope of the appended claim.

What is claimed is:

A steroid of the formula No references cited. 

